Flying High and Getting By
by darkangel9314
Summary: Damon Salvatore has always been an infamous bad boy at his school, but when his latest stunt gets him caught his only option is to join Pages for Places which happens to be run by his crush and the girl who happens to hate him the most. Can they work out their differences and do what's best for the club? Or will Damon's fantasies vs his reality be his downfall
1. Chapter 1

Flying High and Getting By

Chapter 1

There were many feeling in this world that Damon Salvatore could describe however being cross faded and fucking a girl at the same time was not one of those feelings that could be easily explained. He loved the feeling of getting high and drinking at the same time, but there was a feeling of pure content when he threw a girl or two in the mix. He had decided to only include one today because it had been a spur of the moment decision. One that would have gotten him in a lot of trouble if he and the girl he was now fucking were caught. After all having sex on school grounds was already frowned upon, he had no clue how much trouble he would actually be in if any of the school officials found out he was breaking all three of their golden rules. He didn't want to think about that right now, all he really wanted to think about was the moment he was in right now.

He smiled at the girl pushing down the rest of her bra strap watching the rest of the bra cling to her perfect breast. He couldn't believe he had been so lucky. It wasn't everyday that one of the semi popular crowd wanted to screw him. But he would take Caroline Forbes over anyone else anyday. Well excepted the only popular he actually wanted under him, but this was not a time to be thinking about her right now. Espically since she still hadn't forgiven him for screwing her cousin well over two years ago.

Caroline giggled as Damon stuck his hand down her shorts feeling her gathering wetness as his lips collided with hers. He felt her deep moans as he inserted one of his fingers inside of her watching her squirm was without a doubt one of his most pleasurable moments. He just couldn't help himself anymore. He had to be inside her and he had to make it quick the last thing he needed was one of their teachers finding them and calling his parents. After all life at home was rough without the breaking of school rules inserted into the mix.

He shoved Caroline's shorts down as he pulled down his pants and underwear to as far as they would go entering Caroline in one swift movement. He thrusted inside of her as he forgot about everything that had been troubling him over these past few days. He held her on the ground watching as her face twisted in utter pleasure. He always loved that face when it came to the girls he was screwing it was without a doubt one of the second best feelings in the world. Next to getting high naturally.

He felt his climax getting close as he quickened his pace to release. He was almost there he only had a couple more minutes left. However luck was not on his side that day. Before he knew it Caroline's look of pleasure had turned into utter horror as Damon turned his head slightly to see what she had been looking at.

He swore he could have died from embarrassment right there and then as he looked up to see one of their teachers faces staring down at them. Damon groaned as he pulled out of Caroline and got dressed. They were in major trouble now and Damon knew there would be serious consequences to his actions.

Damon kept his eyes firmly planted on the floor concentrating on his shoes as Caroline sat in the principals office explaining herself. He knew that she would not be in trouble because they had already ruled out that she hadn't been drinking and lighting a joint while she was out there, but Damon hadn[t been that fortunate he wouldn't be surprised if they kicked him out right there and then. At least his parents would have an actual reason to beat his ass tonight, but he wouldn't think of that right now. He couldn't think about that right now.

A door opened and Damon looked up. The principals door was still shut tightly but Damon's eyes traveled to the next door as his face went white with shock as if this moment couldn't get any worse. At least he would get to see her face one last time before he got sent to boot camp or something worse by his parents.

Elena Gilbert walked up to the security's desk as he took one last opportunity to look at her perfect assests. He swore that Elena Gilbert was the perfect woman with her dark brown hair an those gorgeous brown eyes that he could just get lost into. Not to mention she had a few other great assests that he loved to look at. After all that girl did have the nicest tits and ass he had ever seen and he hadn't even slept with her.

But alas that idea had been foiled when he had slept with her cousin Katherine instead. Elena had not appreciated it when they had broken up and had been rude to Damon ever since. If only she really knew how much that really turned him on. He would have countless sexual fantasies of them during class and even would right some down. He had ton admit that his favorite time was when he was high because it sparked up his creative genius. But he couldn't think of that right now all he really wanted to think about is why Elena had been sent to the office to begin with.

He turned his head to the desk as he listened in carefully.

"Hey Regina. Principal Lockwood sent for me."

"Ah yes Elena, I heard she had a proposition for you if you'll just take a seat she'll be with you and Mr. Salvatore in a moment."

Elena turned her head sharply to where Damon sat and narrowed her eyes at him. As if she didn;t hate him enough he hated to think what she thought of him now that he was wasting her precious class time. For girls like Caroline that didn't really matter, but he knew they mattered to Elena Gilbert.

Crossing her arms over her chest, Elena made her way over to Damon and looked down on him. He had to admit that from where he sat he did have a very nice look at the cleavage she always tried to hide, but he couldn't think about that right now. He had to concentrate on what she was saying.

"What the hell have you done this time Salvatore?"

Smiling Damon shrugged as her face turned red from anger. He really didn't want Elena to know the pacific. After all she already hated him enough for her cousin that she had always hated, he wondered what she would feel like if she found out that he had been caught screwing one of her best friends that she was actually very fond of.

Taking a deep breath Elena took a seat in the chair next to him and gave him her most nasty looks as they waited for the principal to finish with Caroline. After what seemed like forever Caroline finally made her way out of the office and walked over to Damon completely ignoring Elena as she did.

Caroline got down to where they were eye level and smiled at him.

"Thanks for the good time Damon I really needed that. Call me if you want to finish what we started maybe somewhere a little more private this time." Caroline said giving him a kiss on the lips before she gave a quick hi to Elena and ran off in some other direction that Damon could care less about. What he was really trying to do was ignore the full on death glares that Elena was now giving him. So much for being discrete.

Thankfully the principal had saved him for further embarrassment as she called them into the office. Damon made a beeline for the office as he sat down on the chair waiting for his punishment after all anything would be better than having to listen to Elena bitch for the next hour and a half about how much of a scumbag he truly was.

Damon smiled at principal Carol Lockwood as she gave him a look of disdain. This wasn't the first time Damon had been in her office and if they let this one slid with him he was pretty sure that it wouldn't be his last. After all he had been a troublemaker ever since he had been born and he wasn't about to stop anytime soon. But he had to admit that the lecture he was about to receive was gonna be one of the principals best.

"Damon Salvatore, why am I not surprised to see you here?"

"What can I say Mrs. Lockwood. I was born to be bad."

"You know I don't believe that Mr. Salvatore, but judging from the list of things that you're in here for today there will be major consequences for your actions. I mean drinking on school property, having sex with a fellow student, and the use of drugs are all strictly prohibited and if the school board had it their way you would be expelled as of this moment."

"So why am I still here?"

"Because Mr. Salvatore. I have seen your grades and believe it or not I would hate to waste such potential which is why Ms. Gilbert is here. I have a proposition for both of you,m but only if you both agree to it."

"And what would that be?"

"Have you ever heard of the club Pages for Places Mr. Salvatore?"

At this Elena stiffened, but didn't say a word as Damon and Mrs. Lockwood continued.

"No. I can't say I have. But what does that have to do with me and Elena."

"Elena here is the president of Pages for Places you see they are a club that goes to a writing expo every year, but the funding for their club is being threatened to be cut if they don;t win this year."

"So what do you want me to do about that?"

"I've seen some of the essays you've written in English class Mr. Salvatore and they're quite good. So I've come up with a deal. If Ms. Gilbert and you agree to you joining this club than I won't expel you as long as you don't step out of line again and you help them win. No goofing off. What do you say?"

"Why would I want to join her stupid club?"

"It's not stupid Salvatore it's a great club."

"Is that why you guys haven't won anything Yet?"

Elena's face turned red as Damon smiled he loved getting under that skin of hers.

"Enough! I advise that you take this seriously Mr. Salvatore. You're education is very important to us and perhaps a constructive outlet will do you some good. It would save you quite a few trips to this office not to mention it would give you plenty of things to do and opportunities to get out of the house. So please think about this before your ego gets the best of you."

Damon pondered this for a second as he weighed all the prose and cons of this deal that he just been offered. It would get him closer to Elena and even if she refused his advances it was a way to get him away from the dreaded place he was now calling home. Maybe this plan wouldn't be so bad.

"Alright, I accept. If Elena agrees of course."

Elena bit her lip as she thought about this for quite a while. He really hoped she didn't send him to hell in a hand basket just because she didn't like him.

"Fine. I guess he could join."

"Excellent. Well you two best be getting off to class. I've already sent word to your teachers. And Mr. Salvatore try not to get caught with your pants down anytime soon."

"Well do Mrs. Lockwood."

As Damon and Elena exited the office, Damon was shocked when Elena grabbed him by the collar and shoved him to the wall pressing the full force of her body to his. If she didn't utterly hate him, Damon would have thought this was her way of saying she wanted to fuck him right there and than, but since he knew that this wasn't the case he probably thought she was trying to scare him just a bit. That was find by him because either way she was hot as hell doing it.

"Listen here Salvatore, Mrs. Lockwood might have let you off easy but you will have no such luck with me. Pages for Places is my baby, I started that club fro the ground up and I will not have you ruin it by embarrassing me. So I've come up with a few conditions of my own. First of you will not miss or be late to a single meeting. You will take this as seriously as you would everything else and I mean seriously not your version mine you here me. You will do your best and write until those damn fingers are cramping up and by any circumstances you will not screw one of my best friends again!"

"That's quite the list Ms. Gilbert. But what do you care if I screw your friends. Do you want me all to yourself because I can assure you that I can arrange that."

Elena threw him to the wall and crossed her hands over her chest. God he loved it when she did that.

"Stop fucking around Salvatore. I wouldn't screw you if you were the last guy on this earth. Now do we have a deal or not?"

"What's in it for me?"

"You not getting expelled such be motivation for you enough. Now do we have a deal?"

Damon sighed. "Fine. Whatever you say, but for future reference can I have a list of your friends so I don't accidentally screw one and get myself kicked off the team."

Elena sighed. "You're impossible." she said walking away.

"I wasn't joking."

"I'll give it to you later at practice!" She yelled back as he watched her leave.

Damn that girl was gonna be the death of him as he knew it.


	2. Chapter 2

Flying High and Getting By

Chapter 2

For as long as Damon Salvatore could remember, he had no real issue putting words onto a page that was until the day he had been all but forced to join Pages for Places. He felt it a tad bit unfair that his punishment for skipping class that day had been to do more work than he originally was supposed to, but he guessed that was why they had called it a punishment after all. All Damon knew was that he wouldn't be going there without at least a little bit of a fight.

Sitting down at a nearby tree, Damon rummaged through his bag after school until he found exactly what he was looking for and smiled. He looked around the premise to see if any teachers were there to notice as he pulled out the joint and lighter and proceeded to put the joint to his lips to take a toke. If he was going to be forced to go to this club that was basically dying, he was determined to be at least half way prepared to have a semi decent time.

If Damon had to measure time at that moment he would say that he was halfway through his joint when she came up to him. It seemed as if Damon Salvatore had never really taken the time to appreciate how gorgeous Elena Gilbert really was until that pacific moment. He studied her walking towards him watching the sway of her hips as she kept up with her own pace. Her long straight brown hair wiped around her as her face showed determination to get over to him. Even the hard look on her face that showed way more than just frustration and impatience looked beautiful on him. It wasn't until she was right in front of him did her charm for the moment seemed lost on her.

"There you are, I've been looking everywhere for you."

"Well here I am, you can go back to whatever you were doing now, I'm almost done here and I'll join you afterwards."

"Or you could come with me right now and stop trying to waste my time, I am the leader of this little group you know?"

"As you so kindly remind me, but alas princess I don't take orders from girls like you."

Elena crossed her arms giving him a hard look as she sneered at him.

"How about threats than?"

"You don't seem like the type. Besides I'm pretty sure I can take a scrawny thing like you."

"I'm not trying to fight you, you selfish prick, I'm just so politely reminding you that smoking of any kind is prohibited on campus, so all it would take is one call to our principal to inform him of the problem we have here and your ass is expelled. It wouldn't bother me one bit."

"You wouldn't do that. You need me. Besides a good girl like you doesn't have the balls to mess with a guy like me."

"This club is my baby Damon Salvatore and I won't lose it because a punk ass like you has decided it's not worth saving. Now get your ass up now before I drag you by that pretty boy hair of yours. Don't make it come that far."

"Sheesh don't get you panties in a bunch Gilbert, I'm coming just hold your horses for a second."

Damon put out his joint stuffing it back in his bag for later as Elena turned on her heels making sure her hair slapped him in the face before she walked away expecting him to follow. He promptly rolled his eyes before following her to the library to start his day in hell.

No matter how much Damon bitched through the experience he had to admit that he had no clue how much Elena Gilbert cared about this shit hole of a group. If he didn't have to be here he would care less, but now that he was taking it all in he knew without a reason of a doubt why Elena desperately wanted to keep this group alive in the first place. There was a sort of charm to them that Damon would have never noticed if he had talked to them individually.

Damon lolled his head back as Elena threw back the library doors and inclined her head for him to follow. If she wasn't such a goodie two shoes Damon really thought Elena Gilbert could be one of the most popular and amazing girls in school. It was such a shame that she was such a nark or he would want to hang out with her more often.

"Well here we are, my home away from home."

"You have a funny definition of what the word home means."

"You've never read a book in your life have you?"

"I'm not really much of a reading person."

"Well that explains quite a few things actually."

"Ouch."

Elena sent him one of her best smiles and stopped right in front of him.

"What are you doing?"

Elena's smile grew wider as she pulled something off of the shelf and handed it to Damon.

"What's this?" he said looking at the book back and forth.

"It's a book."

"Okay I know I said I'm not much of a reader, but I know what a book is."

"I know that silly. This right here is my favorite book."

"So your a girl of the classics?"

"Does that really surprise you?"

"No. Not really, but To Kill A Mockingbird defiantly seems like your style."

"You should give it a try I think you'd like it."

"I think I'd be more of a high fantasy kind of guy."

"Fine." she said grabbing the book and putting it on the shelf. "Follow me than."

Damon followed Elena to another shelf where they kept the high fantasy books and handed him one that looked semi interesting.

"The Lord of the Rings. Interesting."

"It sounded like something that you of all people would be interested in."

"Thanks. I'll be sure to check it out."

"I'll believe it when I see it."

Damon shrugged as Elena touched his shoulder leading him to a table where a group of people sat.

"Elena! Finally! We were worried that you had abandoned us." said a girl with caramel skin.

"Oh Bonnie, You know I would never do that to you."

"Who's the cutie that you're dragging over here?"

"I wouldn't necessarily call him cute."

"Ouch. She's in denial, I'm gorgeous."

"Cocky much?" Elena asked lifting up her eyebrows.

"I don't know about cocky, but the ladies do tell me I have a big cock."

"Gross." Elena said slapping him over the head.

"You're the one who started the joke."

Elena started to laugh before taking a look at her group and stopping.

"Let's go ahead and get started. Would you like to introduce yourself to the rest of the group."

"Sounds like a good idea. Well my name is Damon Salvatore and I'm here because this is my punishment for smoking weed on school grounds."

"Awesome." said a guy who Damon knew as Jeremy Gilbert, Elena's little brother.

Elena gave him a harsh look that made him clamp his mouth shut and shrug in his seat. There must be something more there than what meets the eye.

"Anyway, Even though I am here more or less against my will I look forward to working with all of you at some point in the future." he said taking an empty seat next to Bonnie.

"Well now that that's taken care of we can start beginning our latest story outlines for the competition."

Damon raised his hand as the group looked at him.

"Yes, Damon?"

"What's an outline?"

The group and Elena gave him a strange look as she spoke up.

"Didn't they teach you how to outline in English?"

"I always seem to have English right after I've blazed out from my highs."

Elena rolled her eyes.

"Typical. Alright guys go ahead and start your outlines while I give Damon a little extra help."

The group laughed while Elena gestured for Damon to follow her.

Damon didn't know much about the library, but when Elena took him to one of their private rooms that was also sound proof he got a little bit more than excited. She turned to him and narrowed her eyes while opening the door.

"Wipe that smile off of your face."

"What smile?"

"Don't try to play coy with me Damon. And stop doing that eye thing."

"Who know Elena Gilbert was such an expert on body language."

"Whatever. Are we doing this or what?"

"Wow who knew Elena Gilbert knew how to get down."

"Please take what I'm trying to do here seriously or I will go to the principal and tell him that I'm retracting his officer. Trophy or not there are some things even I'm not willing to tolerate."

Damon put his hands up in a surrendering gesture and Elena narrowed her eyes slightly.

"Fine princess we'll do it your way, but if you ever need some fun-"

"I'll remember not to call you. Now come on we have work to do."

"Lead the way my fair lady."

"Please don't ever call me that again."

"Whatever you say."

The room Elena escorted him into was a small room with four blank white walls, a single table, four chairs, and a small window where you could briefly see the outside. If Damon didn't know better he could have sworn that this place could be used for an interrogation room.

"Is this a study room or something that the librarians use to shoot their torture porn?"

"Is everything out of your mouth disgusting? Can you not construct a simple sentence without the use of an insult or a rude comeback?"

"I thought the point of your club was for individual to express themselves in their writing?"

"So you do listen to me?"

"Of course you have a pretty mouth."

Damon felt the sting of the slap before he even knew Elena had done it. His hand flew up to his cheek as Elena's eyes went wide with shock as if she couldn't believe she had been the one to do that. Damn, this girl was defiantly something else.

"Did you just slap me?"

"I-I-"

"I guess the perfect princess isn't so perfect after all."

The shock in Elena's face faded as anger replaced the shock causing her to narrow her eyes until they were merely slits.

"Well maybe if you stop acting like such a fucking douche bag for ten seconds I wouldn't have to drop my perfect facade. Believe it or not I do have a reputation to uphold unlike you."

"Does it ever get tiring?"

"Does what ever get tiring?" Elena asked as she set a couple of sheets of paper out.

"Acting perfect all of the time."

"Why do you think I'm so perfect?"

"Please why wouldn't I think of you as anything less than perfect. You're a straight A student with a list of extracurricular activities including this club and you seem to have the perfect life. Who wouldn't want to be you?"

"You'd be surprised how perfect my life isn't."

"Want to enlighten me?"

"I hardly know you."

"That might help your situation."

"I don't need a person like you in my corner, I have plenty of people who are willing to listen to my life story if I need it."

"And you've actually talked about it?"

"Can we change the subject please? Telling you my life story wasn't exactly apart of the agenda today."

"Fair enough. Now can you please show me how to do this outline that you guys so happily went on about."

"Of course. Let's start you out with a basic outline."

"Sounds like a plan." he said taking a seat in one of the chairs.

"Okay, first things first before you need to know the five basic things about starting a story which are your title, setting, characters, your problem, and your solution."

"Sounds simple enough."

"Actually it's not as simple as you think."

"Please it sounds like a piece of cake to me."

"Oh really what's your story about?"

"Excuse me?"

"If it's not as difficult as you think than what's the main focus of your story."

"Okay fine you got me there. Truth is I have no real idea where to start when it comes to actually getting ideas."

"Well what is it you're interested in? That seems like a good place to start."

"Well obviously I'm into girls, getting high, and skipping class whenever I want."

"Well there is defiantly a ton of stories about those particular subjects. But what about high fantasy?"

"What about it?"

"You showed a particular interest in it when we were talking earlier, have you suddenly changed your mind?"

"No, but just because I'm into fantasy doesn't mean I can write it. "

"Well you never know until you try."

"There's that Elena Gilbert optimism I know so well."

Elena slid the notebook to him and smiled.

"Go ahead. Let's try it. What's going to be your setting?"

"Okay I'll bite, I like medieval times. Does that work?"

"Anything that you want works if you put enough time and research into it."

"Ugh I hardly do homework research, why would I want to do research for this."

"Because it's important for every story period you do to be accurate, so research is always usually best."

"Okay. I guess I can give in this once."

"Great. Now what seems to be the problem in your story?"

"An evil lord has seemed to kidnap the princess of a rival court."

"Seems pretty good. Now what's going to be your solution?"

"I have it in mind, but every great story doesn't reveal isn't conclusion off of the bat."

"I thought you haven't read a book before?"

"Doesn't mean I haven't seem some rather intriguing TV shows."

"You have a fair point there. Fine what about your character?"

"Well I think I might have to work more on a character analysis don't you think?"

"You have to actually have a concept of your characters before you get to your character analyses. So stop stalling."

"Okay. You win. So far all I have is the kidnapped princess, the evil lord, and her knight and shinning armor."

"Sounds like a fair enough start."

"So are you going to give me a character analyses now?"

"That's not until tomorrow. Until than we should really get going."

"It's over already?"

"Yep. The library only gives us an hour per day."

"That doesn't seem long enough."

"It's not, but what else can I do?"

Elena opened the door and turned back to Damon.

"You coming?"

"Of course."

And with that Damon Salvatore ended his day seeing a new side of the maybe not so perfect Elena Gilbert.


End file.
